N-(benzenesulfonyl)-2,2,2-trichloro-N-dodecylacetamide | 1190977-77-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-(benzenesulfonyl)-2,2,2-trichloro-N-dodecylacetamide
• CAS: 1190977-77-5
• 化学式: C₂₀H₃₀Cl₃NO₃S
• 分子量: 470.888
• InChiKey: RAIWCNUTGBHLKV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.3
• 重原子数：
  28
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  62.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(benzenesulfonyl)-2,2,2-trichloro-N-dodecylacetamide 在 五甲基二乙烯三胺 、 copper(l) chloride 作用下， 以 二氯甲烷 为溶剂， 以78%的产率得到N-(benzenesulfonyl)-2,2-dichloro-N-dodecylacetamide
  参考文献：
  名称：

  1,4-Aryl migration under copper(I) atom transfer conditions

  摘要：

  Reaction of N-alkyl-N-(trichloroacetyl)arylsulfonamides with CuCl/amines leads to N-alkyl-N-(dichloroacetyl)-arylsulfonamides via reduction or N-alkyl-aryldichloroacetamides via 1,4-aryl migration with loss of SO2. The ratio of reduction to aryl migration is dependent upon the temperature and the ligand utilised. Along with amide bond hydrolysis these reactions may compete when carrying out slow atom transfer radical cyclisation reactions using sulfonamides. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.07.089
• 作为产物：
  描述：

  N-dodecyl-benzenesulfonamide 、 三氯乙酰氯 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 反应 24.58h， 以55%的产率得到N-(benzenesulfonyl)-2,2,2-trichloro-N-dodecylacetamide
  参考文献：
  名称：

  1,4-Aryl migration under copper(I) atom transfer conditions

  摘要：

  Reaction of N-alkyl-N-(trichloroacetyl)arylsulfonamides with CuCl/amines leads to N-alkyl-N-(dichloroacetyl)-arylsulfonamides via reduction or N-alkyl-aryldichloroacetamides via 1,4-aryl migration with loss of SO2. The ratio of reduction to aryl migration is dependent upon the temperature and the ligand utilised. Along with amide bond hydrolysis these reactions may compete when carrying out slow atom transfer radical cyclisation reactions using sulfonamides. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.07.089

文献信息

• 2-Aryl propionamides via 1,4-aryl radical migration from N-arylsulfonyl-2-bromopropionamides
  作者：Andrew J. Clark、Stuart R. Coles、Alana Collis、David R. Fullaway、Nicholas P. Murphy、Paul Wilson

  DOI：10.1016/j.tetlet.2009.08.125

  日期：2009.11

  Reaction of N-alkyl-N-arylsulfonyl-2-halo-propionamides with pentamethyldiethylenetriamine and either CuBr or CuCl leads to 2-aryl propionamides via initial radical generation, 1,4-aryl migration with loss of SO2 and reduction of the intermediate amidyl radical in 40-99% yields. (C) 2009 Elsevier Ltd. All rights reserved.
• 1,4-Aryl migration under copper(I) atom transfer conditions
  作者：Andrew J. Clark、Stuart R. Coles、Alana Collis、Thomas Debure、Collette Guy、Nicholas P. Murphy、Paul Wilson

  DOI：10.1016/j.tetlet.2009.07.089

  日期：2009.10

  Reaction of N-alkyl-N-(trichloroacetyl)arylsulfonamides with CuCl/amines leads to N-alkyl-N-(dichloroacetyl)-arylsulfonamides via reduction or N-alkyl-aryldichloroacetamides via 1,4-aryl migration with loss of SO2. The ratio of reduction to aryl migration is dependent upon the temperature and the ligand utilised. Along with amide bond hydrolysis these reactions may compete when carrying out slow atom transfer radical cyclisation reactions using sulfonamides. (C) 2009 Elsevier Ltd. All rights reserved.